The Bet

It all started with a bet. It was no secret between Stacy and I about my little kink. We had talked about it in the past, especially in bed after a long, hard session. No matter how much I tried, I kept coming back to the same fantasy. I wanted to watch. I know, I know it's weird, I was even a little weirded out by it, but there was no denying how much it turned me on or how much it turned her on...

Stacy was gorgeous. Young, hot, nice tits and the best ass on the planet. Despite all this she was shy and nervous about showing it off. Oh, I knew she had a wild streak; she had it before we got together, but now, my innocent girlfriend was a bit of an introvert. However, whenever I talked about sharing her, watching her, and having a stranger take her like a dirty slut, her pussy would soak the bed. So I knew I had to do something and I naturally started pushing her towards it.

I tried for months. Like most guys in my situation I started to give up hope that it would become anything more than a fantasy. Then one night, while we were getting ice cream, Stacy brought up a party she was going to with her best friend the next weekend. When I asked Stacy the theme she turned bright red and said,

My dirty mind instantly started turning gears thinking of the possibilities with this. "Ha. Okay, babe, what are you going to wear then?" I said with a smirk.

"I was actually going to match with Jessie, she is wearing a like secretary type outfit," she quickly replied. She had obviously put some thought into this.

"So what does that entail? Short skirt, white button shirt, and heels?" I responded. "Like when we role play sexy CEO?"

"Yes. Just like that. I was thinking that black lace bra and thigh highs too," she said, looking away from me.

Now I was starting to get excited. I couldn't believe she was thinking like this. If she was going to dress like that maybe she was finally ready to try out our fantasy for real.

She looked at me now, biting her lower lip, silently looking for approval, searching my face for some sort of reaction.

Quickly I replied, "Well, if you're going out like that then you better wear the outfit right. If my girlfriend is dressing like a slut then you better be the hottest one there."

Stacy flashed me a grin and said, "Oh yeah, don't worry I was already thinking that. Plus I was going to wear that bright, red, lipstick that you like."

I liked it when she wore it because her lips looked amazing when they were wrapped around my cock and she knew it. Now I knew what she was thinking. She was deliberately doing this to look sexy, but how far was she going to go?

"But anyway it doesn't matter because no guy would want me even dressed up like a hot secretary," she said with a fake sad face.

"Ha! Want to bet! I will bet you anything you could get any guy you wanted to fuck you until you couldn't walk and that's before you are done up. You would barely make it into the house before someone would offer to bend you over," I shouted with a laugh.

"Fine. What's the bet then?" she quickly retorted.

"Okay, you seriously want to bet? Fine. I bet that you could walk into that party and pick any guy you wanted and get him to fuck you," I said, "and if I'm right you've got to blow me for an hour and if I'm wrong I'll buy you a day at the spa."

By the time we got home that night she was so worked up she practically ripped off my clothes. I pushed her down and pulled off her tight jeans while she pulled off her shirt. She had on a bright green bra with a matching thong. I clawed off her underwear and buried my face in her waiting pussy.

She started bucking her hips as I flicked my tongue across her clit and ran it up her slit. I slowly stuck a finger in her pussy, sending a spasm of pleasure through her body. While I thrust my fingers into her wet cunt I furiously sucked on her clit. She grabbed the back of my head, forcing my tongue deeper. I could tell she was getting close. Just as her movements reached their peak she clenched her legs around my head. With a scream her cum splashed across my chin and mouth.

“No more! No more, I can’t take it, I need you in me now.” She moaned.

I needed no further encouragement. I took my rock hard cock and pushed it into her waiting pussy. I grabbed her arms and pinned them over her head as I thrust into her. I started driving deeper into her so that skin slapping was echoing through the apartment.

“You like it rough don’t you, babe? You know this is what is going to happen to you on Friday night,” I said, as I started moving faster, feeling the familiar sign of orgasm. “This is how you’re going to get fucked as a dirty, party girl.”

I quickly flipped her on to her stomach and pressed myself into her again. Her amazing ass bounced in time with my cock. Running my hands up and down her back I could feel her tighten as she came close to cumming for a second time. She arched her back too, letting me penetrate further into her.

“He’s going to bend you over just like this and rail you until you can’t move.”

At those words, Stacy tensed up and released all over my dick. She turned her head and looked back at me with utter lust in her eyes. Stacy pushed herself up onto all fours, thrusting her ass back towards me, begging me to fuck her harder.

“Come on fuck me! Use me like a dirty little slut. I want your cum all over me!” she said through clenched teeth.

My tempo increased to a fever pace as countless dirty images flooded my mind. In a grunt I pulled out and aimed at her back. My cum splattered her body dripping down her ass towards her still wet pussy. I rolled off her and fell across the bed with a sigh of utter exhaustion.

“Wow, I can’t wait until Friday night,” I whispered between heavy breaths.

“Neither can I,” Stacy snorted. ”You may win the bet, but I’m the one who will get my brains fucked out.”

------------------

As Friday night rolled around I sat at the office scrambling to get some last minute work done. Leave it to the boss to give me a big project on the night I finally get to carry out my fantasy. Just as I was packing my things up I got a text from Stacy.

“So lover, what’s the deal? Do you actually want to do this bet? It is okay if you don’t want to. “

Instantly I replied, “Yes. No getting out of it now. “

She quickly responded, “So what are the rules then? What’s the actual bet?”

“The rules are simple. I am proving that you could fuck any guy you want. All you have to do is find a guy you want and then seduce him in whichever way your feminine wiles desire. No matter what you decide to do, you must ask him if he wants to fuck you. You do not have to actually bang him, just get him to say he would. If he says yes then I win the bet and get my blowjob. If he says no then you win and get your spa day.”

Almost as soon as I sent my text I got Stacy’s: “Okay. Deal. ;)”

I knew the night would be interesting.

An hour later I arrived at our apartment just as Stacy and her friend Jessie were leaving, and let me tell you, wow…

They were both dressed like the twin secretaries on one of those movies where most of the dialogue is moans and grunts. Stacy had told me what she was wearing before, but words didn’t do justice compared to seeing it in person.

She had done just a single button on her shirt, letting her lacy black bra show up top, and her stomach with a small stud, down below. Her tight skirt came just a few inches down her thighs. You could just make out the top of her thigh highs peeking out from under her skirt. She had topped off the whole ensemble that bright red lipstick she knew I loved. Stacy oozed sex appeal.

From my expression they could tell they looked good. Stacy wrapped her hands around my neck and pushed her lips to mine. She pulled herself in with a primal growl and bit my lower lip. Moving to the side of my head she kissed my neck.

Brushing her lips ever so lightly against my ear she whispered, “Well, good luck. I hope you win.” With that she released me and sauntered over towards her car. “Love you, baby, I will get back late, don’t wait up.”

Jessie turned to get in the driver's side and shot me a wink. Well, I guess Stacy had a wing girl for the night.

Like I said, I knew it would be interesting.

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The night seemed like it dragged on for hours. Every time I looked at the clock it seemed to be standing still. I would glance at my phone every few moments waiting for any sort of news. I was so horny I couldn’t concentrate on TV, and although I craved a release, I knew I had to wait for some sign.

Around 12:30 I was starting to get tired and it looked like I wouldn’t be hearing from Stacy any time soon. Just as I was getting into bed, my phone vibrated with a text. It was from Stacy.

“Hey babe, how’s your night going?”

I could practically hear the shit-eating grin on her face as she said that. I quickly replied, “How do you think? Tired, horny, nervous, horny, and also a little more horny.”

“Haha, oh I’m sorry babyyy. Want me to make it up to you?” Stacy said. “Switch on your computer and look at your email.”

With a grumble that was born from sexual frustration, I moved over to my laptop and opened my email. In it was an invite to a webchat. Now my curiosity started to grow. What was she doing?

I clicked on the webcam and onto the screen popped Stacy. “Hey, baby! I’m so glad to see you. I have been having the best time. Me and my new friend Mike have been hanging out all night,” she said with a wink and a grin.

I could tell Stacy had had a few drinks by the way she was talking very fast. She always would get super wet when she was drunk.

“Oh yeah, babe, where is this Mike fellow?” I stated sternly, trying to keep a smile from creeping into my face.

“Well let me tell you what I have been doing all night, silly,” Stacy replied. “First we got here and they gave us some drinks. Jessie had run off immediately with some guy she knew to do whatever. You were right though, I wasn’t even halfway through my first beer before this guy saunters over to me and asks me for a dance. He was cute so I said yes and followed him out into the middle of the floor. We started up pretty fast, but he was a terrible dancer and the whole time he was trying to grind his dick into me.”

My own dick twitched at that comment as I tried to contain my own excitement.

“Anyways after that song his friend cuts in and offers to show me how someone actually dances. He was very hot and so I said yes. We started moving to the beat and I found myself grinding my hips into him. One of the dirty dancing songs came on and he twirled me around so my ass was right up against his crotch. He moved perfectly and with each passing sway, he would push into me. By now all I was thinking about was our bet so I decided to play along and push my ass back into him.”

Now I was really turned on. Here was my innocent girlfriend telling me how she was grinding her ass into some stranger’s crotch on the middle of a dance floor.

“I could feel him start to get hard as we moved and it really excited me. Then a slow song came on and he started dancing with me back towards a darker corner of the room. Once we were a little hidden from view I spun around and pushed my chest into his. At this point I could feel his dick through his pants and my pussy was practically on fire. As we danced he slowly pushed his hands lower and was playing with the end of my skirt. He quickly slipped his hand under my skirt and grabbed my ass.”

By now I could see her skirt was a little rumpled and just talking about this was turning her on even more.

“He slowly ran his right hand around my thigh until he was just inches below my pussy. He could obviously tell I was soaking wet. He started walking his fingers up my thigh until he was just a hair away from actually touching it. At this point it was like I was in a trance, but I chickened out and stopped him.”

I groaned with displeasure. Why would she have stopped him? She was just being a tease.

“He introduced himself as Mike, he went to school up here. We laughed and flirted a little ways, but I was so nervous I had to get some air. So him and I walked back to the bar area got a few drinks and then went to sit outside. Even though I was super nervous I was pretty turned on and I couldn’t stop thinking about our bet.”

I snorted, causing her to arch an eyebrow.

“We found a bench a little ways away from the party off in the dark, and started nursing our drinks. I ended up joking with him about the bet between you and I. He told me that he could definitely help me out with it. I laughed it off, but by now I was pretty drunk. Just as I turned to say something to him, he grabbed me and pulled me into him on the bench. He pressed his lips to mine and I let out an involuntary moan. I couldn’t get enough of him and grabbed the back of his head while I pressed my body into him. He was so hot, I melted into right his arms. I felt him reach between my legs and slowly work his way up to my thong. It was happening so fast and I couldn’t do anything to stop it.”

Now my dick was fully erect just thinking about her making out with this guy she barely knew.

“Just as I put my tongue into his mouth he pressed his fingers to my panty-covered slit and it sent a jolt up my body. My pussy soaked itself all over again. He knew I wanted him and with a quick twist slipped his underneath my panties. I arched my hips to give him better access and he pushed his fingers right into my sopping, wet pussy. He started thrusting his fingers in and out of my little cunt, tickling my. He started going faster and reached up to grab my tits. It was too much for me an in a flash I was cumming all over his hand. Just as I came down from my high I heard a giggle and saw another couple watching us from the driveway and knew we had been caught. So we quickly fixed ourselves and went back inside. My panties were covered in my cum and there was no way people weren’t going to notice,” Stacy said, completing her story.

I was so excited, at some point in her story I had cum and I didn’t even realize.

“Oh, Stacy, baby, that is so fucking hot, see I told you that you could do it. I guess I win the bet,” I stated triumphantly.

“Not so fast, lover boy. The bet was to get a guy to fuck me, getting fingered on a bench in the backyard does not count as fucking,” Stacy said with a grin. “And that’s what brings me to why I am on this webcam with you. I figured, as long as you’re quiet you could watch.”

‘Watch what, babe?” I stammered hesitantly.

“Well, baby, I told Mike to go get us some drinks and then meet me up here in fifteen minutes. I asked him to come fuck me.”

Oh boy. Definitely an interesting night.

------------------

Before I could even get in a word of protest Stacy pushed the computer away and hid the webcam where her new lover wouldn’t see. I could hardly contain my excitement as I watched my girlfriend saunter over to the mirror and adjust her outfit. She fixed her hair, straightened her skirt, and flicked off her heels. Just as she had finished reapplying her makeup there was a knock on the door.

Stacy practically ran over to the other side of the room where I couldn’t see and opened the door. I heard some voices, one obviously Stacy, the other must have been Mike. I couldn’t make out what they were saying, but I did hear the door closing.

Stacy let out a little squeal as Mike picked her up and threw her on the bed. Now they had crossed in front of the camera and I could see everything. He pressed himself on top of her with urgent need and they started making out. I saw Stacy’s hands reach up and unbutton his shirt until his bare chest was hanging over her. She reached down and started stroking the growing bulge in the front of his pants.

Mike slipped his hand into Stacy’s shirt and grabbed onto her right breast. He played with her nipple until it was sticking straight up, begging to be sucked on. Suddenly he stopped and stood straight up. With a growl he reached down and ripped off her shirt, flinging buttons all across the room. Stacy let out a gasp of surprise and pleasure.

Mike grabbed her shoulders and slid her off the bed so that she was on her knees. Stacy reached up and pulled off his belt, throwing it across the room in a sexual fury. He reached over and helped her with his button. Quickly, she reached up and tugged his pants down.

Stacy yanked off his boxers letting his cock spring free. She let out a small gasp at its size. It was perhaps the same length as mine but very, very, thick around. Her small hands could barely grip it all the way. This new cock entranced her and for a second I thought she wasn’t going to do anything.

Mike reached down and unclasped her bra letting her tits hang free. Then he slowly directed her towards his waiting member, twitching in anticipation.

“Oh I don’t know, Mike. I don’t think I can fit that all in my mouth, that is such a big cock,” Stacy said nervously.

“Well if you’re going to be a slut and win that bet then you better act like a slut,” Mike said with a grin.

Without another word Stacy’s mouth engulfed the head of his cock. Her red lips stretched to accommodate his impressive girth and for a quick second she flashed her eyes at the camera.

She placed one of her hands at the base and worked her mouth over the head, licking. With her free hand she grabbed his ass and pulled him closer. Her head started bobbing faster up and down his length. She started jerking her hand up and down his shaft as she continued to work as much of his head into her mouth as she could.

She slid her other hand to his balls. Mike let out a groan of pleasure as she tickled him there while simultaneously jerking him into her mouth. Then she flipped his dick up towards his stomach and ran her tongue down the length to his balls. Taking each one in her mouth gently she flicked her tongue back and forth while rubbing her hand on the tip of his.

Suddenly Mike growled, “Enough. I can’t take any more of this. I want your pussy.”

He grabbed her under her arms and lifted her onto the bed. Stacy’s eyes went wide with excitement and she knew what was coming next. Before she could react he pushed her skirt up from her waist, giving him direct access to her waiting cunt. With a tug he pulled aside her g-string and pressed himself into her.

Stacy arched her back and let out a long moan as she felt the first new cock enter her in years. Mike reached over and grabbed her tits with one hand and used his other to grab her waist to pull himself in deeper. He started rhythmically thrusting into her, slowly working his way deeper. Abruptly he pushed his full length into her making her cry out and her whole body shake.

Mike started going faster; slamming his dick in and out of her soaking, wet pussy. He placed both his hands on her waist and started pounding her little cunt for all he had. Stacy wrapped her legs around his back and pulled him into her. She reached her arms around him and grabbed onto his back urging him on with her moans.

Their pace became fervent, as they both got closer to orgasm. In a cry of pure pleasure Stacy closed her eyes and came all over this stranger for the second time that night. Her heat must’ve sent Mike over the edge as he tensed up and slammed his cock in deep as it could go.

Stacy’s eyes went wide as he pumped his cum into her. She moaned in utter lust feeling another man’s cum deep in her pussy. Mike slid his cock from her, covered in a mix of his and her cum. Stacy led out a deep breath and tried to calm her breathing.

Panting, Mike looked at her, and said, “Sorry, I should have asked first I just couldn’t stop you were so hot.”

Stacy looked up at him with glazed eyes, “It is fine. I love it when a guy blows his load in me.”

She glanced down at her pussy, still wearing her lacy g-string. It was covered in cum where Mike had forced his way into her. She reached down and stuck a finger into her dripping cunt, feeling how wet she was. Stacy shuddered with a surge of nerves as she realized what she had just done. She had actually fucked another guy; all while I watched on a webcam.

“Well, I guess I really am a little whore now,” Stacy said to the room with a laugh.

Stacy started to rise from the bed and gather her things when Mike glanced over to her,

“Where do you think you’re going?” Mike said. “I am not done with you yet.”

She looked up at him and saw his cock slowly harden again. He stood her up and pulled her naked body into his. At the same time Stacy reached out and grabbed his still-wet dick, stroking him.

I sat there mesmerized by what I was watching on the computer. I didn’t think my own dick could take any more, but I stiffened once again as I watched Mike slide off Stacy’s g-string and toss it across the room. Stacy unzipped her skirt and tossed it aside as quickly as she could so that she now was in just her thigh highs.

Suddenly he reached to her hips and spun her around. She had her hands on the bed and her ass towards him. Stacy stuck her ass into the air and arched her back to give him easy access to her wet cunt. Mike took the cue and pushed himself into her waiting pussy. With a jolt, he slammed himself into her. The room filled with Stacy’s moans and slapping skin as his balls bounced against her pussy. Stacy’s tits were bouncing in time with her ass as her slutty, wet pussy got fucked from behind.

Mike slid himself in and out of her faster and faster; their breathing getting heavier, their cries more urgent. Stacy reached around and rubbed her clit. Arching her back, Stacy buried her face in the bed while he grabbed her ass and pounded her as hard as he could. The entire bed was rocking back and forth and both of them were covered in a sheen of sweat. Her moans grew louder with each passing moment.

Then Mike pushed her down until she was flat on her stomach with her ass in the air. She tensed up and I saw her once again cum for him; giving him a renewed vigor to stroke into her harder. Stacy must have sensed he was close, so she pulled his cock out and twisted around onto her back. In a grunt Mike’s face twisted and he started to cum. Stacy carefully aimed his cock and splashed his cum all over her chest and stomach.

He collapsed onto the bed, his now softening cock still slick with Stacy’s juices. They both laid there panting on the bed while they waited for the rush to ebb. Mike rose first and started collecting his clothes, stopping to grab Stacy’s still-damp panties, laying on the floor.

“I am taking these are a souvenir. But I am not letting you go tonight. What time do you have to be home?” Mike said as he put on his shirt.

Stacy still lay there on the bed covered in cum and out of breath.

“I don’t have any time to be back,” she replied quietly.

“Well, I live just a street away. After the party, why don’t you come back with me and you can have more of that?”

“Okay, I’ll see.”

With a wink Mike gathered his things and left the room leaving Stacy to gather herself. Once she had her clothes she turned towards the camera and me.

“Well, well, I guess you won the bet sweetie,” she said to me with a sexy voice.

I couldn’t help but notice how good she looked. She had cum all over her tits, and I could see it leaking out from between her legs. There was no way she could walk back through the party without people noticing how thoroughly she had just been fucked. I felt a surge of emotions part jealousy part raw lust as I gazed at her. I wanted her so bad I almost couldn’t control myself; I wanted to drive straight to that party and fuck her for the rest of the night.

“I think I’m going to go stay at Mike’s place, I mean I don’t want to drink and drive after all. I will see you in the morning babe,“ she said, and quickly turned off the webcam.

A few minutes later I got a text,

“Good night, you know I love you.”

Wow. I was glad I let her go to that party.

------------------

Stacy came home the next day wearing someone’s white tee shirt and a pair of running shorts. As soon as she came in the door she threw her arms around me and kissed me deeply. She smelled like sweat, alcohol, and sex and I immediately felt myself start to stiffen.

“I missed you, baby. I love you. Are you mad at me?” she said as she looked up at my eyes.

“Oh, of course not, babe, that was a dream come true thank you so much,” I said quickly. “So what did you do the rest of the night?”

“Oh, well I stayed and drank some more. Jessie ended up going home with a guy she has been sleeping with and Mike had offered me his place. So I went an stayed at his overnight,” she said while looking away from me.

“Oh yeah? And what did you and him do?” I laughed.

“Well what do you think?” She laughed back at me. “I went back to his place and he fucked me twice more then we fell asleep and he then he fucked me again before I left.”

I felt myself grow hard hearing her say it. I reached my hands into her shorts and felt her pussy, still wet with their cum. With a wink she starts walking towards the bedroom stripping off her shirt as she went.

“Come on, lover, I guess I owe you that blowjob,” she said as she looked over her shoulder at me. “Mike said I give the best ones he’s ever had.”

Yeah. I am definitely happy that she went to that party.

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